


Let Me Show Ya Somethin'

by CatWhiskersWithin



Category: Batman - All Media Types
Genre: Batfamily Feels, Brotherly Bonding, I Tried, I really just wanted some Tim and Damian bonding, Other, Please I need it, Tim and Damian in Drag
Language: English
Status: Completed
Published: 2019-02-26
Updated: 2019-02-26
Packaged: 2019-11-05 21:44:04
Rating: Teen And Up Audiences
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 1
Words: 3,072
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/17926901
Author URL: https://archiveofourown.org/users/CatWhiskersWithin/pseuds/CatWhiskersWithin
Summary: Because Damian has to go undercover, in Drag, as per Robin tradition. But he's not going alone, Tim is there to help!





	Let Me Show Ya Somethin'

**Author's Note:**

> I just really enjoy the idea of Tim being great at Drag and getting to teach Dami how to go undercover for the first time in a skirt. Also this was written in a weird stream of consciousness, so sorry if it doesn't make sense. It was never supposed to be this long, its literally just short of 6 pages on my google doc.

Damian and Dick were eating breakfast at the table while Tim was adding ungodly amount of sugar to his coffee and Jason was quietly chatting with Alfred when Bruce came down. He sat at the head of the table and accessed the scene in front of him before turning to face Damian and nodding to himself.  All of the boys took notice but no one said anything as they figured Bruce or maybe Batman would tell them later.

 

After breakfast was over, Bruce called for Damian to go with him to the Batcave, alone. Damian assumed his father was going to praise him for not sending any criminals to the hospital within the past week and a half. Instead, he was wordlessly shoved toward the more secluded part of the cave that contained some undercover ‘costumes’.

  
Bruce directed him to the female clothing with a brief explanation of, “You and Red Robin will be going undercover in a human trafficking ring. He’ll share the details with you later, just pick some clothing that you feel comfortable with and is somewhat age appropriate.” Bruce then turned on his heel and left Damian to his own devices.

 

This is the first time that Damian had ever felt overwhelmed. He had assumed he was trained for anything, turns out his mother forgot to train him in going undercover as a woman. He was slowly going through the clothing that seem to be closest to his size with his face scrunched up.  _ Tt, Father's taste in women’s apparel is truly disappointing. There is nothing suitable… _ Damian did eventually find some leather hot pants and a matching crop top.  _ This ought to be acceptable, now to find Drake. _

 

Damian carried his newfound treasure upstairs to the manor, hoping to get to his room with ease. Of course this was not the case as Dick and Jason were both waiting for him at the entrance to the cave.

 

“You owe me twenty, Dick! I told you Bruce needed him for undercover!” Jason yelled as he slung an arm across Damian’s shoulders while holding out his free hand toward Dick.

 

“Dammit! I knew Bruce left the cave quickly but, like, I didn’t think it was that quick!” Dick retorted while pulling a bill out of his wallet. “Anyways Babybat do you want any help? That looks like a lot… of leather…” he paused. “Are those, by any chance, from the femme side of the costume closet?” Dick asked, tring to swallow some of his laughter down.

 

This meant that Jason didn’t hold any of his back and was on the floor in a matter of seconds. Damian took the opportunity to kick him in his stomach as he went by, he also got a good elbow jab into Dick’s side.  _ Tt, what is the big deal. All of them have played women before. I shall follow the previous Robins’ footsteps, except I will exceed more than any of them!  _ Now determined, Damian went straight to his room. He needed no assistance from Grayson nor Todd and he would prove as much.

 

Two hours later found Tim walking down the hall, fresh out of a shower, to Damian’s room to see how the demon brat was doing. Tim paused outside Damian’s door, listening to a string of quiet curses and apparent thumping. Tim gave a light knock before opening the door. And then he proceeded to chuckle to himself. Damian froze and stared at Tim in horror, he had one pant leg barely over his knee, the other leg bunched at his ankle and the leather tube top twisted horrifically around his torso.

 

Eventually Tim stopped laughing and asked, “Demon what are you wearing? Or attempting to wear?”

 

“Father said to pick something I deemed acceptable. This was the only clothing with any decent form of protection.” Damian sniffed and turned his nose up, trying to redeem what dignity he had left.

 

“Okay, well that's not going to work for us. First, that is the wrong underwear for hotpant,” Tim gestured vaguely to Damian’s boxers. “And second, we need to match and that outfit doesn’t match any of the others. So go ahead and take it off, I’ll be back in 10 minutes with an outfit for you and me. And I’ll teach you, Lord knows Dick and Jason could never.” 

 

And with that Tim left his doorway, closing the door behind him, and leaving Damian to attempt to wrestle himself out of his leather prison. By the time Tim got back, he was out of the pants and struggling to free himself from the tube top. Tim immediately dropped the pile of clothes and makeup on Damian’s bed before rushing to help him out of the top.

 

Once freed, Tim pulled Damian to the bathroom and sat him on the edge of the bathtub, turning on the hot water and grabbing two razors, one pink and one black, two washcloths and two vibrantly pink cans of shaving cream. “First things first, we have got to shave, normally I’d recommend waxing, but since this is supposed to be a short op we’ll shave. It grows back faster that way.” Tim passed Damian the black razor, a washcloth and one of the cans and Damian nodded his affirmation. Tim turned the water off after a fair amount had filled the tub, and dipped his washcloth in the water and started running it over his legs.

 

They spent the next 20 minutes shaving carefully as Tim would show Damian the best way to shave different areas of their legs. Once they were done shaving, Tim took Damian back into his room and tossed him a pair of panties. “From the data that we could grab, this guy is really perverted and likes boys who dress up as girls so, uh, we don't have to  _ tuck _ , our, uh…” 

 

Damian raised an eyebrow as he examined the panties, before looking back to Tim. “Tuck?”

 

“Uh, we’ll talk about that another time,  _ if _ you have to go undercover again, as, like, a  full girl. Anyways go put those on, I have mine already under my shorts.” Tim then turned around and started organizing the clothes and makeup.

 

Damian let out a small cough, and when Tim turned around, Damian’s blush had spread from his face down onto his chest. Tim then tossed him two fake breasts and a bra, “Stick the padding on and then the bra, tell me if you need help.” Tim then began sticking on his fake breasts and clipped the bra in front of him before twisting the bra to its correct position. He then helped Damian clip his bra from behind his back.

 

“Before I help you put on your top and skirt, I’m gonna show you how to do your makeup. This guy make like boys dressed as girls, but the more girl-ish you look the more likely he is to choose us for the night.” Tim called over his shoulder as he carried the makeup into the bathroom. “Trust me, Bruce will probably have you go under again as a girl and this is the most important part of all this. We need to soften all your sharp edges, little demon.”

 

Damian put on a pair of sweats and glared as he followed Tim into the bathroom. “I don’t see how one can soften one’s face with simple powders.” With a roll of his eyes, Damian did as Tim gestured and sat himself on the cushioned stool in front of the vanity. 

 

Tim began pulling out several pallets and a couple sealed bottles of foundation. “These aren’t just ‘simple powders’, demon. They’re some of the nicest make-up, and I’ve had the joy of testing and perfecting my feminine side. You’ll see soon enough. I’m going to show you how I put mine on, and then you’ll follow on your face. Don’t worry about any mistakes, I’ve gotten good at fixing them.”

 

“Tt, as if I would make any mistakes, Drake. Do you take me for a fool?” 

 

“No, but makeup is something that takes time and practice. Unfortunately, we don’t really have a lot of time tonight so just follow along.” Tim started wetting a beauty blender and poured a small amount of foundation onto the back of his hand. 

 

Three hours later, and Tim had finished both his and Damian’s makeup. (At some point he had to take over for the poor boy. He may be able to draw, but ‘painting’ one’s face is an entirely different skill, as the two had learned.) 

 

“Alright, D. I got your wings pretty even, and your lashes should be just about dry. Go ahead and open your eyes, tell me what you think?” Tim said as he stepped out of the Damian’s way to the vanity mirror. 

 

Damian sat shocked at the face that stared back at him. It was a softer face than the hard angles he was used to seeing stare back at him. And his eyes seemed even brighter than normal,  _ I look almost coy, _ he thought to himself. Tim was standing behind him, looking very smug with himself, until he check his watch.

 

“Shit, we have to hurry. It’s 6:23, and he picks his choice at 8:00. We still have to make sure the clothes fit and sit right, not to mention the wigs.” Tim frantically pulled Damian back into  the boy’s room and started tossing pieces of clothing at him. “Alright skirt first, but don’t zip it up, then put on your top, it’ll be easier to tuck in that way.” Tim said as he started pulling on the dress he had grabbed for himself.

 

Damian did as told but questioned, “Why am I in a skirt, and you’re in a dress?”

 

Tim zipped up the dress and turned around to face Damian. “Because, I’m skinnier than you kid. And i’ve worn so many corsets over the years for ops that I have some curves. You don’t, so a skirt and top is gunna give us a better allusion. Not to mention, a dress fits heels better, and I decided that you should really be in flats.” Tim explained as he fidgeted with Damian’s clothing and eventually zipped up the skirt.

 

Tim then dragged Damian back to the bathroom, where some wig caps and two dark colored wigs layed. Tim handed Damian some wig glue, “I assume you know what to do for this?” Damian snatched it, and both boys started getting their wig caps and eventually the wigs on themselves.

 

They ran down the stairs, where the rest of the family was waiting for them. Dick stared, mouth wide open. Barbara gave a smile, as did Stephanie. Duke stared before shaking himself out of it and giving a thumbs up, and Cassandra signed a quick ‘good luck!’ Jason gave a wolf whistle before he too just stared, Bruce gave a nod of approval and Alfred greeted them with a smile and a, “Good evening, young madams. I have the car awaiting you in the front drive of the manor.” Tim and Damian waved goodbye as they headed out into the car.

 

Damian elbowed Tim. Hard. 

 

“Ow! What was that for?!”

 

“They laughed at us, obviously we look ridiculous. This will never pass.” Damian stopped walking out to the car.

 

Tim paused and then faced him. “Damian, no one laughed. They were all there because it’s like a right of passage. First undercover op, especially one where you’re in a skirt and a long wig instead of pants and a hat brings the family together. Not to mention, there is pictures of just about everyone, at least us guys, dressed up as girls. Dick and Jason’s are actually hilarious, I have no idea how they passed.” Tim let out a small giggle before grabbing Damian by the shoulders. “But that's besides the point, we look good Damian. You look good. And we’re going to go get the op done, get dirt on that douchebag, and then Batman and the rest of the crazy bat family is going to come reign hell down on these sickos.” Damian gave a small smile before getting into the back of the car and Tim followed.

 

Alfred dropped them off about 4 blocks away from where the meet-up point was supposed to be. They hurriedly walked over and Tim did a brief run-down with Damian on what was supposed to happen. “This man’s name is Alfonso Aprendechi. He’s supposedly one of the heads of this ring. They mostly focus in human trafficking, a little bit of drug smuggling here and there. I told him that you and I were interested in meeting up with him and earning a couple of bucks. Essentially, we need to act like sugar babies that are desperate for a sugar daddt, okay?” Damian stared at Tim for a few second before he nodded his head. “Okay good, now let me talk to him. And if anyone touches you slap them, but don’t punch. That’ll just end with Red Hood coming in to do a shoot out, and we learn nothing about where they’re keeping the rest of the kids.”

 

They got to the street corner and waited for less than a minute when a discreet town car pulled up to them. The backseat window rolled down. “Tammy? You’re even more pretty in person. And your,  _ sister, _ Dalia, she’s beautiful.”

 

Tim slunk forward and leaned his head into the window a bit, a small smile on his lips. “I’m glad you like us, does this mean we get to go with you?” Tim asked as he trailed a delicate finger down the man’s arm.

 

Alfonso grabbed Tim’s hand and kissed it gently before motioning to the driver to unlock the doors. “Of course, baby. Why don’t you two get in, and I’ll take you back to my place. There’s a big, comfortable bed that I would love to see you two on.” He winked as he carefully pushed the door open.

 

Tim grabbed Damian’s hand and helped him into the car before he got in himself. Tim sat in Alfonso’s lap and whispered, “Sorry, Dalia is a bit shy. It’s her first time out with me, but I couldn’t deny you.” Tim kissed his cheek and shuddered in disgust when he felt Alfonso’s grip tighten on his thigh.

 

The driver started taking them through Gotham’s undergrounds and into the warehouse district near the docs. The entire time Tim made sure the perv didn’t touch Damian, and kept their cover up. Damian spent the time watching and learning from Tim, how to flirt like a girl and keep wandering hands from going too far.

 

When the car pulled up to one of the warehouses the man grabbed Tim and Damian around their waists and walked in with them. Damian followed Tim’s lead and attempted to snuggle into the man’s side as coyly as possible. It seemed to work as the man held a little tighter to Damian as he walked them further into the building, boasting about how great and wealthy he was. It took most of Damian’s self control not to roll his eyes at the man or scoff at what he considered a fortune.

 

They arrived at an office that had large windows overlooking the abandoned factory floor. The man poured them all drinks before handing the cups to Tim and Damian. Tim giggled and took a small sip of the cheap champagne before motioning for the man to sit between him and Damian. When the man made himself comfortable on the couch, Tim pulled out a small taser from under his dress and assisted the man to an unconscious state.

Damian then pulled out a pair of comms and masks from under his skirt and handed one of each to Tim after he put the taser away. “Father, the target is unconscious in the office. We believe the rest of the children are here.” Damian crept over to the windows to look out at the sea of old machinery. He heard the crackle of Tim’s comm unit connecting to the current line.

 

Tim and Damian left the room, Tim holding his taser and Damian holding a small knife that Tim had helped him hide in his clothes earlier. They soon ran into Nightwing and the Red Hood on the floor of the factory. 

 

“B says there might be a hidden basement/tunnel area from prohibition. We just need to find out how to get down there.” Nightwing said as he shone his flashlight around some of the machinery.

 

The four boys split off into pairs again, but this time Damian insisted on going with Tim. This of course left Nightwing confused and Red Hood chuckling at said confusion. After almost 20 minutes of searching Damian spotted a somewhat clean looking hatch on the ground. They opened it and heard what sounded like distant voices. Tim told the others where to find the hatch before following Damian down.

 

They followed the tunnel toward a somewhat distant light, slinking in the shadows as much as possible, in case there were any guards posted. They thankfully found none, and instead found almost thirty kids between twelve and twenty in various closet-like rooms. They helped the kids back towards the opening of the tunnel and up to where Batman and the others were helping to hand out blankets and water.

 

After all the kids were out and taken care of, the bat family left and Tim and Damian were picked back up by Alfred. As soon as they were in the car, Tim removed his heels and helped Damian with taking off his wig. By the time they got back to the Manor, all that was left for them to do was remove their makeup and change clothes.

 

Tim brought the wipes to Damian’s room and they silently scrubbed their faces with a countless amount of wipes. After their makeup was off Damian and Tim stared at each other through the mirror before they both started laughing. 

 

They spent the rest of the night talking about the awful one-liners they had to endure, and how wealthy the guy thought he was compared to how much each of their individual net worth’s were. For the first time, Tim and Damian had connected on something, and Tim had earned more respect from Damian than anyone had thought possible.


End file.
